Sodium hydride → HCID 67111911, compound

HRID 1177601Notes

Reaction equation

HRID 1177601 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:28][OH:29])[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2.Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]1)[N:13]=2)[CH2:28][O:29][CH2:31][C:32]([O:34][CH3:35])=[O:33]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetate2×HCID 44601272HCID 44601272, compound

Product 1

HCID 67111911HCID 67111911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.015 mL, 0.35 mmol) was added to a light yellow solution of (3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methanol (0.110 g, 0.29 mmol) in DMF (3.00 mL); the color changed to dark brown. The reaction mixture was treated with methyl 2-bromoacetate (0.032 mL, 0.35 mmol), and the color changed to green, then yellow, and then became cloudy. After 15 min, additional methyl 2-bromoacetate (0.032 mL, 0.35 mmol) was added, and after 15 min, the reaction mixture was quenched with NH4Cl, extracted with EtOAc, and the organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 15-20% EtOAc/hexanes to give methyl 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyloxy)acetate. MS (ESI) m/z: calculated: 448.1; Observed: 449.0 (M++1).

Workup

  1. waitafter 15 min
  2. customthe reaction mixture was quenched with NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 15-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-35f2a99f16164e3b8fac558d37abff78
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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