Bromoacetyl chloride → (S)-4-(2-(2-bromoacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

HRID 1776604Notes

Reaction equation

HRID 1776604 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].[Br:28][CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[Br:28][CH2:29][C:30]([O:10][C@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[CH2:8][C:7]1[C:6]([Cl:26])=[CH:5][N+:4]([O-:27])=[CH:3][C:2]=1[Cl:1])=[O:31]

Participants

4

Reactant 2

HCID 89602Bromoacetyl chlorideHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 86679564(S)-4-(2-(2-bromoacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (500 mg, 1.2 mmol) was dissolved in DCM (15 ml), and TEA (180 mg, 1.8 mmol) and 2-bromoacetyl chloride (243 mg, 1.55 mmol) were added. The mixture was stirred at RT for 2 hours, then was diluted with DCM (50 ml) and washed with HCl 1N (2×). The organic phase was dried over Na2SO4 and evaporated under vacuum, obtaining a crude (550 mg) containing the title compound (MS/ESI+ 541.17 [MH]+) which was employed in the next step without any further purification.

Workup

  1. washwashed with HCl 1N (2×)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated under vacuum
  4. customobtaining a crude (550 mg)

Sources & evidence

ORD record
ord-86068be5c7e94c87af7f79a7f13c3584
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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