Triphenylphosphine → 4-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

HRID 633244Notes

Reaction equation

HRID 633244 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Cl:9][C:10]1[CH:31]=[C:30]([S:32]([CH2:35][CH2:36][CH2:37]O)(=[O:34])=[O:33])[CH:29]=[CH:28][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:16]=1)=[O:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:8][CH2:37][CH2:36][CH2:35][S:32]([C:30]1[CH:29]=[CH:28][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH:16]=2)=[O:13])=[C:10]([Cl:9])[CH:31]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 58614673HCID 58614673, compound

Product 1

HCID 668778424-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

115 mg of NBS was added to a solution of 200 mg of 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(3-hydroxypropylsulfonyl)benzamide and 169 mg of triphenylphosphine in 3 mL of dichloromethane at 0° C. The reaction mixture was stirred at 0˜5° C. for 1 h. The mixture was diluted with dichloromethane, washed with H2O, dried (MgSO4) and evaporated. Purified by prep TLC plate (60% ethyl acetate/hexane) to afford 4-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. 60 mg of 4-(3-bromopropylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide and 111 mg of cesium carbonate in 0.5 mL of DMF were heated to 100° C. in a sealed microwave reactor for 20 min. The reaction mixture was evaporated, and the product was purified on reverse phase HPLC to yield 4-(allylsulfonyl)-2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 448.0 (M)+.

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurified by prep TLC plate (60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3753c25d24c34baa8e9b2ea7e177d7a6
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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