Boron tribromide → HCID 57039022, compound

HRID 1420745Notes

Reaction equation

HRID 1420745 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[C@@:14]([OH:16])([CH3:15])[C:13]([CH3:18])([CH3:17])[O:12][C:11]3[CH:19]=[CH:20][C:21]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32]C)[CH:27]=4)(=[O:25])=[O:24])=[CH:22][C:10]2=3)[CH:5]=[CH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[C@@:14]([OH:16])([CH3:15])[C:13]([CH3:18])([CH3:17])[O:12][C:11]3[CH:19]=[CH:20][C:21]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=4)(=[O:25])=[O:24])=[CH:22][C:10]2=3)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57151075HCID 57151075, compound

Product 1

HCID 57039022HCID 57039022, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,4R)-4-(2-Chloropyrimidin-4-yl)amino-3,4-dihydro-3-hydroxy-6-(3-methoxyphenyl)sulphonyl-2,2,3-trimethyl-2H-benzo[b]pyran (0.23 g) (see Preparation 19) was dissolved in dichloromethane (25 ml) (the flask was fitted with a calcium chloride drying tube) and boron tribromide (1 ml) was added. The mixture was stirred at room temperature for 24 hours and a precipitate was formed. The dichloromethane was decanted off, the solid taken up in 1N aqueous sodium hydroxide and washed with ethyl acetate. The aqueous phase was acidified to give a gum which was collected and dried under reduced pressure at 70° C. to yield (3S,4R)-4-(2-chloropyrimidin-4-yl)amino-3,4-dihydro-3-hydroxy-6-(3-hydroxyphenyl)sulphonyl-2,2,3-trimethyl-2H-benzo[b]pyran (0.123 g) as a white solid, m.p.>280° C. LRMS m/z=475 (m)+.

Workup

  1. additionwas added
  2. customa precipitate was formed
  3. customThe dichloromethane was decanted off
  4. washwashed with ethyl acetate
  5. customto give a gum which
  6. customwas collected
  7. customdried under reduced pressure at 70° C.

Sources & evidence

ORD record
ord-895854b603444e91a2c0f710b6d0e60e
Source dataset
uspto-grants-2000_06
Patent number
US06071938

Reaction notes

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