Ditert-butyl phosphate → HCID 67001773, compound

HRID 558076Notes

Reaction equation

HRID 558076 reaction equation
[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([Cl:17])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:18])[C:5]([CH2:19][C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29]Cl)[N:21]=2)=[CH:4][CH:3]=1.[C:31]([O:35][P:36]([O-:43])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([CH3:34])([CH3:33])[CH3:32]>CC#N>[C:39]([O:38][P:36](=[O:37])([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])[O:43][CH2:29][N:22]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:28]2[C:20]([CH2:19][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[C:7]([O:8][C:9]3[CH:10]=[C:11]([C:12]#[N:13])[CH:14]=[C:15]([Cl:17])[CH:16]=3)[C:6]=2[F:18])=[N:21]1)([CH3:42])([CH3:41])[CH3:40]

Participants

4

Reactant 2

HCID 4191557Ditert-butyl phosphateHCID 67001223HCID 67001223, compound

Product 1

HCID 67001773HCID 67001773, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

step 2—To a mixture of 16 (1.28 g, 2.54 mmol), di-tert-butylphosphate (1.06 g, 5.08 mmol), in MeCN (70 mL) was added Ag2O (0.59 g, 2.54 mmol) and the resulting mixture was stirred for 1 d at RT. The resulting mixture was filtered through CELITE®, the filtrate was evaporated and the crude product purified by SiO2 chromatography eluting with a MeOH/DCM gradient (0 to 1% MeOH) to afford 1.1 g of phosphoric acid 3-[4-bromo-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-benzyl]-pyrazolo[3,4-b]pyridin-1-ylmethyl ester di-tert-butyl ester (18)

Workup

  1. filtrationThe resulting mixture was filtered through CELITE®
  2. customthe filtrate was evaporated
  3. customthe crude product purified by SiO2 chromatography
  4. washeluting with a MeOH/DCM gradient (0 to 1% MeOH)

Sources & evidence

ORD record
ord-1dbb22a6a1ee4aacbadbe287cf9630a8
Source dataset
uspto-grants-2011_11
Patent number
US08063028B2

Reaction notes

Loading…