Boron tribromide → HCID 178508262, compound

HRID 1452766Notes

Reaction equation

HRID 1452766 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]3[S:15][C:14]([NH2:17])=[N:13][C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]3[S:15][C:14]([NH2:17])=[N:13][C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178489152HCID 178489152, compound

Product 1

HCID 178508262HCID 178508262, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring suspension of 3-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine (100 mg, 0.41 mmol) in CH2Cl2 (2 mL) at −78° C. was added a 1 M solution of BBr3 in CH2Cl2 (2.1 mL, 2.1 mmol) dropwise. The reaction mixture was slowly warmed up to room temperature overnight, then it was quenched with water, and the reaction mixture was neutralized to pH 6 with 1 N aqueous NaOH. The resulting precipitate was filtered, washed with water, and dried in vacuo to afford 70 mg (74% yield) of 3-(4-hydroxyphenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine as an off-white solid. 1H-NMR (d6-DMSO) δ: 9.8 (broad s, 1H), 7.57 (broad s, 2H), 7.42 (d, 2H), 6.85 (d, 2H); HPLC/MS m/z: 233.0 [MH]+.

Workup

  1. customit was quenched with water
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-211fbf0fc2e9449884d821d939320b54
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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