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Dimethylformamide → 5-(2-benzyl-2H-indazol-6-yl)-7H-pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1973004
Notes
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Reaction equation

HRID 1973004 reaction equation
Br[C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9]([NH2:11])=[N:8][CH:7]=[N:6]2.[CH2:12]([N:19]1[CH:27]=[C:26]2[C:21]([CH:22]=[C:23](B3OC(C)(C)C(C)(C)O3)[CH:24]=[CH:25]2)=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:12]([N:19]1[CH:27]=[C:26]2[C:21]([CH:22]=[C:23]([C:2]3[C:10]4[N:5]([NH:6][CH:7]=[N:8][C:9]=4[NH2:11])[CH2:4][CH:3]=3)[CH:24]=[CH:25]2)=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 585298655-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 711343115-(2-benzyl-2H-indazol-6-yl)-7H-pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 38%

Reagents, catalysts & solvents

2
HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A stirred mixture of 5-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.47 mmol), 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (188 mg, 0.56 mmol), sodium carbonate (119 mg, 1.13 mmol), N,N-dimethylformamide (4 mL) and water (0.3 mL) was degassed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (54 mg, 0.04 mmol) was added, and the reaction was irradiated in a microwave reactor at 150° C. for 15 minutes. The reaction mixture was filtered through Celite®, the pad washed with methanol, and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane and 1N aqueous hydrochloric acid. The dichloromethane extracts were washed with 5% aqueous sodium bicarbonate solution, then brine, dried (anhydrous sodium sulfate); filtered and concentrated in vacuo to afford 61 mg (38% yield) of yellow solid. 1H-NMR (CD2Cl2): δ 8.04 (d, 1 H), 7.86 (s, 1 H), 7.77 (dd, 1 H), 7.75 (d, 1 H), 7.65 (d; 1 H), 7.40-7.32 (m, 5 H), 7.21 (dd, 1 H), 6.77 (d, 1 H), 6.91 (br s, 2 H), 5,61 (s, 2 H). MS: LC/MS (+esi), m/z=341 [M+H]. RT=2.44 min.

Workup

  1. customwas degassed with nitrogen
  2. customthe reaction was irradiated in a microwave reactor at 150° C. for 15 minutes
  3. filtrationThe reaction mixture was filtered through Celite®
  4. washthe pad washed with methanol
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was partitioned between dichloromethane and 1N aqueous hydrochloric acid
  7. washThe dichloromethane extracts were washed with 5% aqueous sodium bicarbonate solution
  8. dry with materialbrine, dried (anhydrous sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ef18e9bf90e45bf9d94b31c1333cfd1
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431695B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes