Triethylamine → 7-[(6-Chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1986648Notes

Reaction equation

HRID 1986648 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:18][O:19][C:20]([C:22]1[S:26][C:25]2[C:27]([NH2:31])=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:18][O:19][C:20]([C:22]1[S:26][C:25]2[C:27]([NH:31][C:6]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:8])=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 45089769Methyl 7-amino-1-benzothiophene-2-carboxylate

Product 1

HCID 577224537-[(6-Chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl esterYield 68%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloronicotinic acid (1.5 eq) and triethylamine (2.0 eq) in CH2Cl2 (5 mL) was added BopCl (2.0 eq). After 15 min, 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (87 mg) in CH2Cl2 and 4-dimethylaminopyridine (DMAP) (1.0 eq) were added to the reaction solution above. The reaction was stirred at room temperature 12 h. The reaction was then diluted with EtOAc, and washed with NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to give a crude material which was purified by flash chromatography on silica gel (20%-50% EtOAc/hexane) to provide 100 mg (68%) of the desired 7-[(6-chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester as a light yellow solid.

Workup

  1. washwashed with NaHCO3 solution and brine
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude material which
  6. customwas purified by flash chromatography on silica gel (20%-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-97913e13830a40e3b398e9413a0d80c9
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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