Water → HCID 178430307, compound

HRID 1024187Notes

Reaction equation

HRID 1024187 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](I)=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[C:23]([O:27][C:28](=[O:47])[N:29]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[C:30]1[CH:35]=[CH:34][C:33]([CH:36]=[O:37])=[C:32]([F:38])[N:31]=1)([CH3:26])([CH3:25])[CH3:24].O>O1CCCC1>[C:23]([O:27][C:28](=[O:47])[N:29]([C:30]1[C:35]([CH3:34])=[C:36]([OH:37])[C:33]([C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[N:6]([Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])[CH:7]=2)=[C:32]([F:38])[N:31]=1)[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)([CH3:25])([CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 497589601H-Pyrrolo[2,3-B]pyridine, 1-[(1,1-dimethylethyl)dimethylsilyl]-3-iodo-HCID 59593274HCID 59593274, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 178430307HCID 178430307, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 1-(tert-butyl-dimethyl-silanyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine (66, 0.53 g, 0.0015 mol) and tetrahydrofuran (15.0 mL), under an atmosphere of nitrogen at −20° C., was added isopropylmagnesium chloride (0.78 mL, 2.0M in tetrahydrofuran). The reaction was allowed to warm to 0° C. (around 80 minutes), then cooled to −20° C., followed by addition of (4-Chloro-benzyl)-(6-fluoro-5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (65, 0.200 g, 0.55 mmol) in tetrahydrofuran (6.0 mL). The reaction was allowed to warm to room temperature in 1 hour, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a yellow solid (67, 0.20 g, 61.1%). MS (ESI) [M+H+]+=597.4.

Workup

  1. temperaturecooled to −20° C.
  2. temperatureto warm to room temperature in 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% ethyl acetate in hexane
  9. customto give a yellow solid (67, 0.20 g, 61.1%)

Sources & evidence

ORD record
ord-b565dfd11bb444a290218892d58dce67
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

Loading…