Imidazole → HCID 67004374, compound

HRID 2095675Notes

Reaction equation

HRID 2095675 reaction equation
[Br:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][N:5]([CH3:7])[CH:6]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.C(Cl)Cl>CN(C)C1C=CN=CC=1>[Br:1][C:2]1[C:3]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 24229713(4-Bromo-1-methyl-1H-pyrazol-3-yl)methanol

Product 1

HCID 67004374HCID 67004374, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of (4-bromo-1-methyl-1H-pyrazol-3-yl)methanol (100.0 mg, 0.5235 mmol), tert-butyldimethylsilyl chloride (236.7 mg, 1.570 mmol), 4-dimethylaminopyridine (12.79 mg, 0.1047 mmol), 1H-Imidazole (106.9 mg, 1.570 mmol) and DCM (40 mL, 700 mmol) was stirred at rt for 1 h. The material was transferred to a separatory funnel and partitioned between DCM and water. The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 2% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. MS (ES+): m/z=305.06/307.06 (100/100) [MH+]. HPLC: tR=1.82 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. customThe material was transferred to a separatory funnel
  2. custompartitioned between DCM and water
  3. washeluting with 2% EtOAc/hexanes
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-33d46395f4114bdd883ab7c77e5653ae
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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