Triethylamine → 1-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-ethanone

HRID 1433160Notes

Reaction equation

HRID 1433160 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]([N:18]([CH2:22][CH:23]=[CH2:24])[C:19](=[O:21])[CH3:20])=[C:6](Br)[CH:5]=1)(=[O:3])[CH3:2].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CC#N.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:19]([N:18]1[C:7]2[C:6](=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[C:9]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=2)[C:23]([CH3:24])=[CH:22]1)(=[O:21])[CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 57934833N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-N-allyl-acetamide

Product 1

HCID 579348431-(1-Acetyl-6-benzyloxy-3-methyl-1H-indol-5-yl)-ethanoneYield 54%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-acetyl-5-benzyloxy-2-bromo-phenyl)-N-allyl-acetamide (0.662 g, 1.65 mmol), P(o-tolyl)3 (0.028 g, 0.092 mmol) and triethylamine (0.34 ml, 2.24 mmol) in MeCN (15 ml) was flushed with nitrogen, followed by the addition of a Pd(OAc)2 (0.005 g). The reaction was microwaved for 500 sec. at 150° C. The crude mixture was diluted with EtOAc, washed with water and dried over MgSO4. Purification by column chromatography in hexane/EtOAc (1:1) afforded (0.283 g, 54%) a cream solid. LC/MS: RT=2.742 min. 322 (MH+), 344 (MNa+), 280 (MH+-Ac).

Workup

  1. customThe reaction was microwaved for 500 sec
  2. customat 150° C
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customPurification by column chromatography in hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-df7fb2c0567241dcb0490c145ab4a670
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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