Sodium hydride → 1-Bromo-3-dimethoxyphosphorylpropane
Reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9]OC1C=C2C(=CC=1)N(CC1C=CC=CC=1)C(Br)=C2CC(N)=O)(=[O:6])[O:4][CH3:5].[Br:32]C1N(CC2C=CC=CC=2)C2C(C=1CC(N)=O)=CC(O)=CC=2.[H-].[Na+]>>[CH3:5][O:4][P:3]([CH2:7][CH2:8][CH2:9][Br:32])(=[O:6])[O:2][CH3:1]Participants
4
Procedure
[3-[[3-(2-Amino-2-oxoethyl)-2-bromo-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester. Using the procedure described in Example 81, Part A, 1.35 g (3.8 mmol) of 2-bromo-5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide was reacted with 170 mg (4.2 mmol) of NaH/mineral oil and then 970 mg (4.2 mmol) of (3-bromopropyl)phosphonic acid dimethyl ester to give a product that was chromatographed on silica gel (eluted with a gradient, 1% MeOH/methylene chloride→3% MeOH/methylene chloride). There was obtained 520 g (27% yield) of 3-[[3-(2-amino-2-oxoethyl)-2-bromo-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester, melting approximately at 100° C. after crystallizing from methylene chloride/ether.
Sources & evidence
- ORD record
- ord-86bd25e488264fcf82bb6d6cc054fc61
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06252084B1
Reaction notes
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