Lithium borohydride → HCID 86270544, compound

HRID 2177568Notes

Reaction equation

HRID 2177568 reaction equation
[Cl:1][C:2]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][C:9]2[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:13]=[N:14][C:8]=2[CH:7]1[C:21](OCC)=[O:22])=[O:5].[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[C:29]([C:30]([F:31])([F:33])[F:32])=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][C:9]2[N:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:13]=[N:14][C:8]=2[CH:7]1[CH2:21][OH:22])=[O:5]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86271945HCID 86271945, compound

Product 1

HCID 86270544HCID 86270544, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 26 (0.10 g, 0.21 mmol) in THF (10 mL) at −78° C. was added lithium borohydride (0.02 g, 1.08 mmol). After 14 h the reaction was quenched with 1 N NaOH and extracted with DCM (3×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.07 g, 76%). MS (ESI): mass calculated for C21H17ClF3N3O2, 435.1. m/z found 436.1 [M+H]+.

Workup

  1. customAfter 14 h the reaction was quenched with 1 N NaOH
  2. extractionextracted with DCM (3×25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b34ba70a1d8d4cd98d19aa449a358ba3
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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