Dichloromethane → 3-methyl-3-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonate

HRID 1962682Notes

Reaction equation

HRID 1962682 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]([N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=[CH:25][C:18]=23)[CH:14]=[N:13]1)([CH3:11])[CH2:8][CH2:9][OH:10].C(Cl)Cl>>[CH3:1][S:2]([O:10][CH2:9][CH2:8][C:7]([CH3:6])([N:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:31])[CH3:32])[CH:24]=[CH:25][C:18]=23)[CH:14]=[N:13]1)[CH3:11])(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 574775823-methyl-3-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]butan-1-ol

Product 1

HCID 574775843-methyl-3-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonateYield 90.9%

Procedure

TEA (38.0 μL, 0.000273 mol) and methanesulfonyl chloride (21.1 μL, 0.000273 mol) were added sequentially to a solution of 3-methyl-3-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]butan-1-ol (prepared as in Example 58) (81 mg, 0.00020 mol) in DCM (4 mL, 0.05 mol) at 0° C. The reaction mixture was held at this temperature for 1.5 hours, then was quenched by the addition of water. The reaction mixture was extracted with DCM four times. The combined extracts were dried over sodium sulfate, filtered and concentrated to afford crude 3-methyl-3-[4-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonate (87 mg). MS (ES): 479 (M+1).

Workup

  1. customwas quenched by the addition of water
  2. extractionThe reaction mixture was extracted with DCM four times
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e3299d5590345a79b561161ebd8d4e5
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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