Dichloromethane → (R)-3-(7-chloro-4-(chloromethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132444Notes

Reaction equation

HRID 132444 reaction equation
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26]O)=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:28]CCl.C(N(C(C)C)CC)(C)C.CS(Cl)(=O)=O>>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26][Cl:28])=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59732062(R)-3-(7-chloro-4-(hydroxymethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

Product 1

HCID 59732079(R)-3-(7-chloro-4-(chloromethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

Procedure

(R)-3-(7-chloro-4-(hydroxymethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate (6.5 g, 16.72 mmol) in dichloromethane (100.0 ml, 1554 mmol) was added Diisopropylethyl amine (2.59 g, 20.06 mmol) followed by methanesulfonyl chloride (1.433 ml, 18.39 mmol). After 2 h, the reaction mixture was quenched with aqueous NaHCO3, dried (Na2SO4) and the solvent was removed. MS (ESI) 407 (M+H); Rf=1.69.

Workup

  1. customthe reaction mixture was quenched with aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-92737ef3b6ae49668ea43e6fb4f565b9
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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