Carbon tetrabromide → HCID 67111838, compound

HRID 1177479Notes

Reaction equation

HRID 1177479 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26]O)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>C(Cl)Cl>[Br:48][CH2:26][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[S:9][C:10]3[C:15]([N:16]=2)=[CH:14][CH:13]=[C:12]([C:17]2([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:19][CH2:18]2)[N:11]=3)=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 44601272HCID 44601272, compound

Product 1

HCID 67111838HCID 67111838, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of (3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol (2.05 g, 5.45 mmol), triphenylphosphine (1.64 mL, 7.08 mmol) in DCM (25 mL) at 0° C. under N2, carbon tetrabromide (0.634 mL, 6.53 mmol) was added. The reaction mixture was allowed to warm up to ambient temperature. The crude reaction mixture after 1 h, was concentrate in vacuo and purified by silica gel chromatography to afford 2-(4-(bromomethyl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine. MS (ESI) m/z; calculated: 438.0; Observed: 438.9 (M++1).

Workup

  1. customThe crude reaction mixture after 1 h
  2. concentrationwas concentrate in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-5c348c57424e4ed2af1ad446cfdcccc3
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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