Boron tribromide → HCID 19595300, compound

HRID 612471Notes

Reaction equation

HRID 612471 reaction equation
B(Br)(Br)[Br:2].[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16]C)[CH2:12][N:11]([NH:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[CH2:10][CH2:9]2>ClCCl>[BrH:2].[F:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[OH:16])[CH2:12][N:11]([NH:18][C:19]1[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=1)[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19595141HCID 19595141, compound

Product 1

HCID 19595300HCID 19595300, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (8.8 g) was added dropwise to a solution of 6-fluoro-7-methoxy-2-(4-pyridinylamino)-1,2,3,4-tetrahydroisoquinoline (2.9 g) in dichloromethane (200 mL) at -78° C. The dry ice bath was removed, and the suspension was stirred at ambient temperature for 3 hrs. The reaction mixture was cooled to -78° C., and methanol (100 mL) was added. The mixture was stirred at ambient temperature for 1 hr and concentrated in vacuo. The residue was washed with methanol/ethyl ether and recrystallized from 2-propanol/ethyl acetate to give 0.61 g (17%) of product, mp 244-245° C. (dec).

Workup

  1. customThe dry ice bath was removed
  2. temperatureThe reaction mixture was cooled to -78° C.
  3. additionmethanol (100 mL) was added
  4. stirringThe mixture was stirred at ambient temperature for 1 hr
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with methanol/ethyl ether
  7. customrecrystallized from 2-propanol/ethyl acetate

Sources & evidence

ORD record
ord-6b5bd79ca8b543018d8dfc7005c109a2
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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