Methyl iodide → HCID 72195295, compound

HRID 510309Notes

Reaction equation

HRID 510309 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:30]([CH3:31])=[CH:29][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]4[C:26]([CH3:27])=[CH:25][N:24]([CH3:28])[C:21]4=[N:22][CH:23]=3)[S:17][C:13]=2[C:12]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C)=CC2N=C(C3C=C4C(C)=CNC4=NC=3)SC=2C=1C1C=CC(Cl)=CC=1)C(OC)=O)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[C:1]([O:5][C@@H:6]([C:11]1[C:30]([CH3:31])=[CH:29][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[C:20]4[C:26]([CH3:27])=[CH:25][N:24]([CH3:28])[C:21]4=[N:22][CH:23]=3)[S:17][C:13]=2[C:12]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86699819HCID 86699819, compoundHCID 86699839HCID 86699839, compound

Product 1

HCID 72195295HCID 72195295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate: To a solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)benzo[d]thiazol-6-yl)acetate (12 mg, 0.022 mmol) in DMF (5 mL) was added cesium carbonate (11 mg, 0.033 mmol). The reaction solution was stirred at room temperature for 5 minutes, iodomethane (4.7 mg, 0.033 mmol) was added. The reaction solution was stirred for 30 minutes and quenched with water. Volatiles were removed and the residue partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to give crude product which was purified by chromatographic column to afford the desired product. LCMS-ESI+: calc'd for C30H30ClN3O3S: 548.17 (M+H+); Found: 548.4 (M+H+).

Workup

  1. stirringThe reaction solution was stirred for 30 minutes
  2. customquenched with water
  3. customVolatiles were removed
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give crude product which
  10. customwas purified by chromatographic column

Sources & evidence

ORD record
ord-9448b4d8c4a84b5e9fd1b2b7c5c3024d
Source dataset
uspto-grants-2015_08
Patent number
US09096586B2

Reaction notes

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