Water → HCID 86721482, compound

HRID 869617Notes

Reaction equation

HRID 869617 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:37]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([C:20]([C:22]3[N:26]4[CH:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[CH:30][C:25]4=[N:24][C:23]=3[O:35][CH3:36])=[O:21])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].[BH4-].[Li+].O>C(O)C.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:37]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH:20]([OH:21])[C:22]3[N:26]4[CH:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[CH:30][C:25]4=[N:24][C:23]=3[O:35][CH3:36])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14]

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 86721483HCID 86721483, compound

Product 1

HCID 86721482HCID 86721482, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

[step 5] (E)-2-{3-fluoro-8-[2-methoxy-7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbonyl)dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (0.100 g, 0.197 mmol) obtained in step 4 was dissolved in ethanol (0.985 mL) and THF (0.985 mL), lithium borohydride (0.44 g, 1.2 mmol) was added, and the mixture was stirred at room temperature for 3 hr. The reaction was discontinued with water, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (E)-2-(3-fluoro-8-{hydroxy[2-methoxy-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (100 mg, 100%).

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96afca8035cb408292be606302cda58b
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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