Diiodomethane → HCID 56940823, compound

HRID 1844051Notes

Reaction equation

HRID 1844051 reaction equation
C(ON=O)CC(C)C.I[CH2:10][I:11].NC1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][N:19]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][C:29]=3[C:30]([F:33])([F:32])[F:31])[C:20]2=[O:23])=[CH:15][C:14]=1[F:34].C(OCC)(=O)C>C1COCC1.CCCCCC.[Cu]I>[F:34][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:10]=1[I:11])[C:20](=[O:23])[N:19]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:29]=1[C:30]([F:31])([F:33])[F:32])[CH2:18][CH2:17]2

Participants

8

Reactant 4

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 8857Ethyl AcetateHCID 66803632HCID 66803632, compound

Product 1

HCID 56940823HCID 56940823, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

Isoamylnitrite (0.4 mL, 3.2198 mmol), diiodomethane (0.4 mL, 5.36 mmol) and CuI (203.9 mg, 1.07 mmol) were added to a stirred solution of 7-amino-6-fluoro-2-(4-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (I-79b: 350 mg, 1.07 mmol) in dry THF (10 mL). The resulting mixture was stirred for 1 hour at 70° C. The reaction was monitored by TLC (40% ethyl acetate in hexane). The reaction mixture was concentrated to yield the crude product. Purification by column chromatography on silica gel (30% ethyl acetate in hexane), followed by preparative HPLC afforded 15 mg of the product (10% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto yield the crude product
  3. customPurification by column chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-710dd530951f46028bf0b4dc159df33f
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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