Dimethylformamide → HCID 86691734, compound

HRID 1426942Notes

Reaction equation

HRID 1426942 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([CH:22]=[O:23])=[C:15]3[N:14]=2)[CH:7]=1.Br[CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH2:26][CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([CH:22]=[O:23])=[C:15]3[N:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 86691733HCID 86691733, compound

Product 1

HCID 86691734HCID 86691734, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-5-(2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (159 mg, 0.487 mmol), tert-butyl 2-bromoethylcarbamate (131 mg, 0.585 mmol), potassium carbonate (202 mg, 1.46 mmol) and DMF (1 mL) was combined in a sealed vessel and stirred at ambient temperature overnight and then at 60° C. for 3 hours. After diluting with DCM (20 mL), the reaction was filtered through Celite®, concentrated and purified by reverse-phase column chromatography, eluting with 0-70% acetonitrile/H2O to provide (R)-tert-butyl 2-(4-fluoro-2-(1-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)phenoxy)ethylcarbamate (198 mg, 86.6% yield) as yellowish solid. MS (apci) m/z=370.4 (M+H-Boc).

Workup

  1. customwas combined in a sealed vessel
  2. waitat 60° C. for 3 hours
  3. filtrationthe reaction was filtered through Celite®
  4. concentrationconcentrated
  5. custompurified by reverse-phase column chromatography
  6. washeluting with 0-70% acetonitrile/H2O

Sources & evidence

ORD record
ord-ce394533e63441ae94cc85801f2a3caf
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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