Triethylamine → HCID 17981650, compound

HRID 2252081Notes

Reaction equation

HRID 2252081 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:20]([CH:21]4[CH2:23][CH2:22]4)[C:19](Br)=[N:18][C:17]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:32])(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH3:33][Si:34]([C:37]#[CH:38])([CH3:36])[CH3:35].C(N(CC)CC)C>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:20]([CH:21]4[CH2:23][CH2:22]4)[C:19]([C:38]#[C:37][Si:34]([CH3:36])([CH3:35])[CH3:33])=[N:18][C:17]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:32])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 17981779HCID 17981779, compound

Product 1

HCID 17981650HCID 17981650, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Combine 1-isopropylsulfonyl-2-amino-6-(1-(cyclopropyl)-2-(bromo)-4-(2-fluorophenyl)-imidazol-5-yl)-benzimidazole (0.332 g, 0.64 mmol), trimethylsilylacetylene (0.36 mL, 2.56 mmol), tetrakis(triphenylphosphine)-palladium (0.150 g, 0.128 mmol), triethylamine (2 mL) and dimethylformamide (4 mL) and heat to 70° C. for 18 hours. Cool to ambient temperature and remove solvents under reduced pressure. Purify the residue on silica gel eluting with acetonitrile/dichloromethane mixtures to provide the title compound (0.295 g). MS(ES+): m/z=536.2 (M+H)+

Workup

  1. customremove solvents under reduced pressure
  2. customPurify the residue on silica gel eluting with acetonitrile/dichloromethane

Sources & evidence

ORD record
ord-c98cb1997e3a497198f3cfb658122b2d
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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