1,2-Dimethoxyethane → HCID 86662083, compound

HRID 1959402Notes

Reaction equation

HRID 1959402 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.CC1(C)C(C)(C)OB([C:18]2[N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)O1.[C:35]([O-:38])([OH:37])=O.[Na+].C1(P([C:53]2[CH:58]=[CH:57]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:59][C:60]([O:63][C:64](OC(OC(C)(C)C)=O)=[O:65])([CH3:62])[CH3:61].[CH2:74](COC)OC>O.CCOC(C)=O.O.CN(C1C=CN=CC=1)C.[Pd]>[C:58]([O:37][C:35]([N:9]([C:64]([O:63][C:60]([CH3:62])([CH3:59])[CH3:61])=[O:65])[C:3]1[C:2]([C:18]2[N:19]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:7][C:6]([Br:8])=[CH:5][N:4]=1)=[O:38])([CH3:57])([CH3:53])[CH3:74]

Participants

11

Reactant 6

HCID 80711,2-DimethoxyethaneHCID 11776TriphenylphosphineHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 6200042-Amino-3,5-dibromopyrazineHCID 46739113tert-Butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Product 1

HCID 86662083HCID 86662083, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 962WaterSolventHCID 22728543Water ethylacetateSolvent

Procedure

A mixture of 3,5-dibromopyrazin-2-amine (200 mg, 0.7908 mmol), tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-1-carboxylate (271.4 mg, 0.7908 mmol), NaHCO3 (199.3 mg, 2.372 mmol) and palladium; triphenylphosphane (45.69 mg, 0.03954 mmol) in dimethoxyethane (2.000 mL) and water (1.000 mL) was heated at 120° C. in the microwave for 10 minutes. The reaction was diluted with EtOAc/water and the layers separated. The aqueous layer was extracted further with EtOAc (2×), dried (MgSO4) and concentrated in vacuo. The residue was taken up in DCM (5 mL), treated with BOC anhydride (517.7 mg, 544.9 μL, 2.372 mmol) and DMAP (9.661 mg, 0.07908 mmol) and allowed to stir overnight at ambient temperature. The reaction was concentrated in vacuo and the resultant residue was purified on silica gel by flash column chromatography (0-10% EtOAc/Petrol) to afford the product as a bright yellow solid (254 mg, 55% Yield). 1H NMR (DMSO) d 1.33 (18H, s), 1.53 (9H, s), 6.90 (1H, s), 7.26 (1H, m), 7.38 (1H, m), 7.58 (1H, m), 8.21 (1H, m) 8.56 (1H, s); MS (ES+) 590.89

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. concentrationThe reaction was concentrated in vacuo
  6. customthe resultant residue was purified on silica gel by flash column chromatography (0-10% EtOAc/Petrol)

Sources & evidence

ORD record
ord-354d89c9f2b74216b7d047b8cda17128
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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