Water → HCID 58529667, compound

HRID 1973010Notes

Reaction equation

HRID 1973010 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8](Br)[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[F:25][C:26]1[CH:51]=[CH:50][CH:49]=[CH:48][C:27]=1[CH2:28][N:29]1[C:37]([NH2:38])=[C:36]2[C:31]([CH:32]=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:34]=[CH:35]2)=[N:30]1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.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>[NH2:1][C:2]1[C:7]2=[C:8]([C:33]3[CH:34]=[CH:35][C:36]4[C:31]([CH:32]=3)=[N:30][N:29]([CH2:28][C:27]3[CH:48]=[CH:49][CH:50]=[CH:51][C:26]=3[F:25])[C:37]=4[NH2:38])[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 58529501HCID 58529501, compoundHCID 59231971HCID 59231971, compound

Product 1

HCID 58529667HCID 58529667, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of tert-butyl 4-(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate (0.5 g, 1.26 mmol) in DMF (15 mL) was added 2-(2-fluorobenzyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazol-3-amine (0.695 g, 1.89 mmol), solid Na2CO3 (0.4 g, 3.79 mmol) and water (1.9 mL). The solution was degassed for 10 min and tetrakis(triphenylphosphine)palladium(0) (0.146 g, 0.126 mmol) was added and the mixture was degassed for another 10 min. The mixture was heated at 110° C. for 1 h 15 min and then cooled to rt. The mixture was filtered through a plug of Celite® and the filtrate was concentrated. The crude purified using an ISCO® instrument using 40-100% ethyl acetate in hexanes. LC-MS [M+H]+=557.2, RT=2.65 min.

Workup

  1. customThe solution was degassed for 10 min
  2. customthe mixture was degassed for another 10 min
  3. temperaturecooled to rt
  4. filtrationThe mixture was filtered through a plug of Celite®
  5. concentrationthe filtrate was concentrated
  6. customThe crude purified

Sources & evidence

ORD record
ord-26d11e9e3d8e4144b7bb4e54e653fa67
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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