1-Bromo-3,3-dimethylpentan-2-one → HCID 68854483, compound

HRID 229463Notes

Reaction equation

HRID 229463 reaction equation
[P:1]([O:21][CH3:22])([O:19][CH3:20])([O:3][C:4]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[NH:10][N:9]=1)=[C:5]([CH3:7])[CH3:6])=[O:2].Br[CH2:24][C:25](=[O:31])[C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28]>>[P:1]([O:21][CH3:22])([O:19][CH3:20])([O:3][C:4]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]([CH2:24][C:25](=[O:31])[C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])[N:9]=1)=[C:5]([CH3:7])[CH3:6])=[O:2]

Participants

3

Reactant 2

HCID 128223071-Bromo-3,3-dimethylpentan-2-oneHCID 68852077HCID 68852077, compound

Product 1

HCID 68854483HCID 68854483, compound

Procedure

The title compound was prepared from 1-(6-methoxy-1H-indazol-3-yl)-2-methylprop-1-en-1-yl dimethyl phosphate from Method I Step B of Example 1 and 1-bromo-3,3-dimethylpentan-2-one from the above using a procedure similar to described in Method I Step C of Example 1. It was purified on RP-HPLC using 30-100% MeCN gradient without TFA to give colorless solid after lyophilization. 1H NMR (CDCl3, 500 MHz) δ 7.70 (d, 9.0 Hz, 1H), 6.86 (dd, 2.1 & 8.9 Hz, 1H), 6.48 (d, 2.1 Hz, 1H), 5.29 (s, 2H), 3.86 (s, 3H), 3.56 (d, 11.3 Hz, 6H), 2.02 (d, 2.5 Hz, 3H), 1.82 (d, 3.5 Hz, 3H), 1.74 (q, 7.5 Hz, 2H), 1.28 (s, 6H), 0.94 (t, 7.6 Hz, 3H). NOE difference spectrum from irradiating 5.29 ppm singlet showed positive NOE at 6.48 ppm doublet and 1.28 ppm singlet. LC-MS: 3.48 min. (m/Z=313.2, 461.2, 439.2).

Workup

  1. customIt was purified on RP-HPLC
  2. customto give colorless solid after lyophilization
  3. customNOE difference spectrum from irradiating 5.29 ppm singlet
  4. custom3.48 min. (m/Z=313.2, 461.2, 439.2)

Sources & evidence

ORD record
ord-4d41d1c21c0e44b1bac2218d6fb4c87e
Source dataset
uspto-grants-2009_07
Patent number
US07563816B2

Reaction notes

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