Boron tribromide → HCID 10193700, compound

HRID 1992307Notes

Reaction equation

HRID 1992307 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[C:27]([CH3:28])=[CH:26][O:25][C:13]=4[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=4)[N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.B(Br)(Br)Br>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:12]4[C:27]([CH3:28])=[CH:26][O:25][C:13]=4[N:14]=[C:15]([C:17]4[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=4)[N:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10287090HCID 10287090, compound

Product 1

HCID 10193700HCID 10193700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1H-indazol-5-yl)-2-(3-methoxyphenyl)-5-methylfuro[2,3-d]pyrimidin-4-amine (50.0 mg, 0.13 mmol) in CH2Cl2 (20 ml) cooled to −78° C. was added BBr3 (0.7 mL, 2.83 mmol, 1M solution in CH2Cl2) drop-wise. The mixture warmed to rt and was stirred overnight. The reaction was quenched with water and the organic and aqueous phases were separated. The organic layer was dried and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (gradient from 20% to 80% EtOAc/hexane) to afford are product (8.4 mg, 17.5%). HPLC/MS: (M+H)+ 358.1 m/z. Retention time (LC-MS)=3.01 min. 1H NMR (DMSO-D6): 8.54(s, NH); 8.11 (d, 1H); 8.07(s, 1H); 7.75(m, 3H); 7.60(d, 1H); 7.47(d, 1H); 7.20(t, 1H); 6.83(m, 1H).

Workup

  1. customThe reaction was quenched with water
  2. customthe organic and aqueous phases were separated
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (gradient from 20% to 80% EtOAc/hexane)
  6. customto afford

Sources & evidence

ORD record
ord-3885ce6ff5b1457bb21f5827f480e205
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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