tert-Butyl acetate → HCID 71209175, compound

HRID 1912604Notes

Reaction equation

HRID 1912604 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[C:10]2=[N:11][C:12]([CH3:22])=[C:13]([C@H:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18])[C:14]([I:15])=[C:9]2[CH:8]=[CH:7]1.C(O[C:31]([CH3:34])([CH3:33])[CH3:32])(=O)C.Cl(O)(=O)(=O)=O>>[C:31]([O:21][C@@H:16]([C:13]1[C:14]([I:15])=[C:9]2[CH:8]=[CH:7][N:6]([CH2:5][C:4]3[CH:23]=[CH:24][C:25]([F:26])=[C:2]([F:1])[CH:3]=3)[C:10]2=[N:11][C:12]=1[CH3:22])[C:17]([O:19][CH3:20])=[O:18])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 71209350HCID 71209350, compound

Product 1

HCID 71209175HCID 71209175, compoundYield 78%

Procedure

To a solution of (S)-methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (660 mg, 1.328 mmol) in tert-butyl acetate (15 mL, 111 mmol) was added dropwise in ˜5 min perchloric acid (0.456 mL, 5.31 mmol) (70% reagent) and the mixture was stirred at RT for 1 h. The mixture was carefully quenched with saturated NaHCO3/water and extracted with EtOAc. The organic phase dried (Na2SO4), concentrated, and purified by column chromatography to provide (S)-methyl 2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (551 mg, 1.032 mmol, 78% yield) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.27 (s, 9 H), 2.74 (s, 3 H), 3.70 (s, 3 H), 5.40 (d, J=2.15 Hz, 2 H), 5.76 (s, 1 H), 6.36 (d, J=3.51 Hz, 1 H), 6.92-7.17 (m, 4 H); LCMS (m/z) ES+=529 (M+1).

Workup

  1. customThe mixture was carefully quenched with saturated NaHCO3/water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-ab93fe74b0ec43e7b1aa0819d60e359c
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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