Sodium borohydride → HCID 68276152, compound

HRID 1400313Notes

Reaction equation

HRID 1400313 reaction equation
[F:1][C:2]([F:24])([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[F:23])[C:3]([NH:5][CH2:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[BH4-].[Na+].ClC1C2C(=CC=CC=2)C=CC=1OCC(C)(NCC1SC=CC=1)C>C1COCC1>[F:24][C:2]([F:1])([O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[F:23])[CH2:3][NH:5][CH2:6][C:7]1[O:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 59054370HCID 59054370, compoundHCID 68276186HCID 68276186, compound

Product 1

HCID 68276152HCID 68276152, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A microwave vial was charged with 2,2-difluoro-2-[(1-fluoronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)acetamide (60 mg, 0.18 mmol), sodium borohydride (16 mg, 0.41 mmol) and 2 mL of dry THF. To this mixture, a solution of 12 (51 mg, 0.20 mmol) in 1 mL of dry THF was added. The vial was sealed and placed in the microwave reactor and irradiated for 30 min at 110° C. until the starting materials had been completely consumed as judged by TLC (petroleum ether/ethyl acetate 80:20). The mixture was evaporated under reduced pressure and the crude was purified by preparative HPLC to afford 2,2-difluoro-2-[(1-fluoronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine as orange oil (53 mg, 91% yield).

Workup

  1. customThe vial was sealed
  2. customirradiated for 30 min at 110° C. until the starting materials
  3. customhad been completely consumed
  4. customThe mixture was evaporated under reduced pressure
  5. customthe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-6defbabff79b446da9a8c5efd9197ba3
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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