Triethylamine → N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2-(thiophen-2-yl)acetamide

HRID 1191330Notes

Reaction equation

HRID 1191330 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)=[O:13].[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][C:27](O)=[O:28].CCN(CC)CC>C(Cl)Cl.N#N>[Br:20][C:16]1[CH:15]=[C:14]([C:12]([C:3]2[CH:4]=[C:5]([O:10][CH3:11])[C:6]([O:8][CH3:9])=[CH:7][C:2]=2[NH:1][C:27](=[O:28])[CH2:26][C:22]2[S:21][CH:25]=[CH:24][CH:23]=2)=[O:13])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 7148514(2-Amino-4,5-dimethoxy-phenyl)-(3-bromo-phenyl)-methanone

Product 1

HCID 66849274N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2-(thiophen-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 947NitrogenSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2-amino-4,5-dimethoxyphenyl)(3-bromophenyl)methanone (5 g, 14.9 mmol) in dry DCM (125 mL) was added thiophen-2-ylacetic acid (2.54 g, 17.9 mmol) and Et3N (6.77, 66.9 mmol) at 0° C. in N2. 10 minutes later, POCK (3.4 g, 22.31 mmol) was added dropwise at 0° C. in N2. The reaction mixture was stirred for 1 hour at 0° C. and then quenched with saturated NaHCO3, and neutralized to pH=8. The mixture was exacted with ACM (30 mL×3). The combined organic layer was dried over anhydrous MgSO4, filtered and concentrated under vacuum to afford N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2-(thiophen-2-yl)acetamide. MS (M+H)=460 and 462.

Workup

  1. customquenched with saturated NaHCO3
  2. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f6e5b460fdec4f8bb7b766f39a88414e
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

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