Trimethyl phosphite → HCID 86618181, compound

HRID 229467Notes

Reaction equation

HRID 229467 reaction equation
Br[CH:2]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11]([C:20](=[O:25])[C:21](Br)([CH3:23])[CH3:22])=[N:10]1)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[P:26]([O:31]C)([O:29][CH3:30])[O:27][CH3:28]>>[P:26]([O:27][CH3:28])([O:29][CH3:30])([O:8]/[C:3](/[C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:2]\[N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[C:11]([C:20]([O:25][P:26]([O:29][CH3:30])([O:27][CH3:28])=[O:31])=[C:21]([CH3:23])[CH3:22])=[N:10]1)=[O:31]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 86618182HCID 86618182, compound

Product 1

HCID 86618181HCID 86618181, compound

Procedure

The title compound was prepared from 1-bromo-1-[3-(2-bromo-2-methylpropanoyl)-6-methoxy-1H-indazol-1-yl]-3,3-dimethylbutan-2-one from Step A above and trimethyl phosphite using the method in Method I Step B of Example 1. It was purified by RP-HPLC using 10-80% MeCN gradient without TFA. 1H NMR (CDCl3, 500 MHz) δ 7.68 (d, 8.9 Hz, 1H), 6.865 (dd, 2.1 & 8.9 Hz, 1H), 6.71 (d, JH-P=3.0 Hz, 1H), 6.67 (d, 2.0 Hz, 1H), 3.89 (s, 3M), 3.63 (d, JH-P=11.2 Hz, 6H), 3.36 (d, JH-P=11.6 Hz, 6H), 2.02 (d, JH-P=2.5 Hz, 3H), 1.88 (d, JH-P=3.4 Hz, 3H), 1.38 (s, 9H). LC-MS: 3.26 min. (m/Z=407.1, 533.0, 555.0). It was noted that a faster-eluting undesirable isomeric side-product was also obtained during this reaction.

Workup

  1. customIt was purified by RP-HPLC
  2. custom3.26 min. (m/Z=407.1, 533.0, 555.0)
  3. customwas also obtained during this reaction

Sources & evidence

ORD record
ord-5ad17cc66fe940d3b1c25d6778e9a561
Source dataset
uspto-grants-2009_07
Patent number
US07563816B2

Reaction notes

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