Triethylamine → HCID 10287178, compound

HRID 1581475Notes

Reaction equation

HRID 1581475 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([NH2:12])[S:8][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>C1COCC1.CN(C1C=CN=CC=1)C>[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:12][C:9]2[S:8][C:7]3[C:6]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:11]=3[CH:10]=2)=[O:32])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 11402593HCID 11402593, compound

Product 1

HCID 10287178HCID 10287178, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (4-methoxy-7-phenyl-benzo[b]thiophen-2-yl)-amine (100 mg, 392 mmol) in THF (5 ml) with triethylamine (0.049 ml, 0.9 eq.) and DMAP (5 mg, 0.1 eq) was stirred together at 0° C. under an argon atmosphere. To this was slowly added 4-fluorobenzoyl chloride (0.038 ml, 314 mmol, 0.8 eq.) and the mixture stirred to 20° C. over 2 h. The mixture was then evaporated to dryness and chromatographed over silica gel eluting with a gradient of heptane/EtOAc (6:1 to 2:1). The product fractions were pooled and evaporated to afford the title compound (74 mg, 50% yield) as a yellow solid MS: m/e=378.3 (M+H+).

Workup

  1. customThe mixture was then evaporated to dryness
  2. customchromatographed over silica gel eluting with a gradient of heptane/EtOAc (6:1 to 2:1)
  3. customevaporated

Sources & evidence

ORD record
ord-395d3627d0d3453f971b43d33ec0f626
Source dataset
uspto-grants-2004_05
Patent number
US06730670B2

Reaction notes

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