Sodium triacetoxyborohydride → HCID 11407042, compound

HRID 1768030Notes

Reaction equation

HRID 1768030 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][C:13]([CH3:15])=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.N1CC=C([N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=3)[CH:24]=[CH:23]2)CC1.C(O[BH-](O[C:42](=O)[CH3:43])OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]=[C:8]([CH2:12][CH:13]([N:22]3[CH2:43][CH:42]=[C:25]([C:24]4[C:25]5[C:30](=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)[NH:22][CH:23]=4)[CH2:24][CH2:23]3)[CH3:15])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 23614432HCID 23614432, compoundHCID 236144341-(7-Methoxy-1-benzofuran-3-yl)propan-2-one

Product 1

HCID 11407042HCID 11407042, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

3-{1-[2-(7-methoxy-1-benzofuran-3-yl)-1-methylethyl]-1,2,3,6-tetrahydro-4-pyridinyl}-6-fluoro-1H-indole was prepared by generally following the procedure outlined in example 41, step 2, starting from the 1-(7-methoxy-1-benzofuran-3-yl)acetone (204 mg, 1 mmol) and 3 (1,2,3,6-tetrahydro-4-pyridinyl)-6-fluoro-1H-indole (216.0 mg, 1 mmol) in 1,2-dichloroethane (100 ml) and acetic acid (1 ml), sodium triacetoxyborohydride (422 mg, 2 mmol). The product was purified by silica-gel column chromatography by eluting it with 80% ethyl acetate:hexane. Brown solid; Yield: 60 mg (14%); 405 (M+H); 1HNMR (400 MHz, CDCl3): δ 8.31 (broad, s, 1H, NH); 7.92˜6.88 (m, 7H); 6.25 (s, 1H); 3.85 (s, 3H), 3.50˜2.60 (m, 10H); 1.03˜1.05 (d, J=8.0 Hz, 3H).

Workup

  1. customThe product was purified by silica-gel column chromatography
  2. washby eluting it with 80% ethyl acetate

Sources & evidence

ORD record
ord-9669c439cfcb400c80e2aa745d1519ae
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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