Benzyltriphenylphosphonium bromide → Ethyl 3-(2-Phenylethenyl)indole-2-carboxylate

HRID 982033Notes

Reaction equation

HRID 982033 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O.[Br-].[CH:18]1([CH2:24][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>>[C:18]1([CH:24]=[CH:1][C:3]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 2734970Benzyltriphenylphosphonium bromideHCID 5107764ethyl 3-formyl-1H-indole-2-carboxylateHCID 20068889(Cyclohexylmethyl)triphenylphosphonium bromide

Product 1

HCID 53837799Ethyl 3-(2-Phenylethenyl)indole-2-carboxylateYield 73%

Procedure

Using the procedure of Example 121 but replacing the resultant compound of Example 98 with the resultant compound of Example 97 and replacing the resultant compound of Example 120 with benzyltriphenylphosphonium bromide gave the desired compound in 73% yield after silica gel chromatography using 4:1 hexane/ethyl acetate. 1H NMR (CDCl3) δ 1.49 (t,J=7 Hz,3H), 4.48 (q,J=7 Hz,2H), 7.2-7.3 (m,2H), 7.35-7.45 (m,5H), 7.60 (br d,J=8 Hz,1H), 8.07 (d,J=16 Hz,1H), 8.16 (d,J=8 Hz,1H), 8.88 (br,1H). Mass spectrum: (M+H)+ =292.

Sources & evidence

ORD record
ord-9fc8fd91084e422fa11a57f3d61f1d82
Source dataset
uspto-grants-1991_02
Patent number
US04994477

Reaction notes

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