Boron tribromide → HCID 58466291, compound

HRID 335870Notes

Reaction equation

HRID 335870 reaction equation
C[O:2][C:3]1[C:8]2[O:9][C:10]3[C:15]([C@@:16]4([CH2:20][O:19][C:18]([NH2:21])=[N:17]4)[C:7]=2[CH:6]=[C:5]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[N:4]=1)=[CH:14][C:13]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[CH:12][CH:11]=3.B(Br)(Br)Br>C(Cl)Cl>[NH2:21][C:18]1[O:19][CH2:20][C@:16]2([C:7]3[CH:6]=[C:5]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[NH:4][C:3](=[O:2])[C:8]=3[O:9][C:10]3[C:15]2=[CH:14][C:13]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:12][CH:11]=3)[N:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67383505HCID 67383505, compound

Product 1

HCID 58466291HCID 58466291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (S)-1-methoxy-3,7-di(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (15 mg, 0.034 mmol) in 5 mL of dry CH2Cl2 at rt was added boron tribromide (1 M in CH2Cl2, 1.0 m in DCM (0.34 mL, 0.343 mmol) and the resulting suspension was stirred at rt for 2 h. The reaction was quenched with half saturated NaHCO3 (50 mL) and extracted with EtOAc (3×25 mL). The combined organics were dried over sodium sulfate, filtered and evaporated to dryness. Purification by silica gel chromatography (CH2Cl2/MeOH=100:10 to 100:12 to 100:15 to 4:1) gave (S)-2′-amino-3,7-di(pyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-1(2H)-one.

Workup

  1. customThe reaction was quenched with half saturated NaHCO3 (50 mL)
  2. extractionextracted with EtOAc (3×25 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification by silica gel chromatography (CH2Cl2/MeOH=100:10 to 100:12 to 100:15 to 4:1)

Sources & evidence

ORD record
ord-194fcc5c7e6e4890898de6da57f012b6
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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