Acetic Acid → 6-Chloro-5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acid methyl ester

HRID 1882247Notes

Reaction equation

HRID 1882247 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([C:17]3[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:18]=3[NH:19]2)=[C:15]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH:28]=2)[CH:14]=1)=[O:12].CC(O)=O>C(Cl)Cl>[CH3:9][O:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([C:17]3[CH:25]=[C:24]([CH3:26])[CH:23]=[N:22][C:18]=3[NH:19]2)=[C:15]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[CH:28]=2)[C:14]=1[Cl:1])=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 588801605-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acid methyl ester

Product 1

HCID 588801136-Chloro-5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acid methyl esterYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
32 °C

Procedure

N-Chlorosuccinimide (79 mg, 0.59 mmol) was added to a solution of Compound 132 (220 mg, 0.54 mmol) in CH2Cl2 (3 mL) with HOAc (1 mL) at r.t. The reaction was stirred for 18 h at 32° C. and was then concentrated in vacuo. Purification by prep-HPLC gave 88 mg (37%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 14.20 (br s, 1H), 8.23 (s, 1H), 8.11-8.19 (m, 2H), 8.00 (s, 1H), 7.87 (t, 1H, J=7.6 Hz), 7.74 (d, 1H, J=7.6 Hz), 7.28 (s, 1H), 4.01 (s, 3H), 3.23 (q, 2H, J=7.2 Hz), 2.37 (s, 3H), 1.34 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C22H19ClN2O4S, 443, 445; found 443, 445.

Workup

  1. concentrationwas then concentrated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-fe247aab2c6a4e0d90651cfd5167f31a
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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