Methyl iodide → HCID 23435575, compound

HRID 277856Notes

Reaction equation

HRID 277856 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[C:23]4[CH:24]=[CH:25][C:26]([C:28]5[NH:29][C:30]([C:33]#[N:34])=[CH:31][CH:32]=5)=[CH:27][C:22]=4[C:21]([CH3:36])([CH3:35])[O:20][CH:19]3[CH3:37])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:38](=O)([O-])[O-].[K+].[K+].IC.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:33]([C:30]1[N:29]([CH3:38])[C:28]([C:26]2[CH:25]=[CH:24][C:23]3[N:18]([C:16]([O:15][CH2:14][CH:12]4[C:13]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)=[O:17])[CH:19]([CH3:37])[O:20][C:21]([CH3:36])([CH3:35])[C:22]=3[CH:27]=2)=[CH:32][CH:31]=1)#[N:34]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6097028Ammonium SulfateHCID 23435592HCID 23435592, compound

Product 1

HCID 23435575HCID 23435575, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9H-fluoren-9-ylmethyl-6-[5-cyano-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate (0.4 g, 0.8 mmol) and potassium carbonate (1.5 g) in anhydrous DMF was treated at ambient temperature under a blanket of nitrogen with iodomethane (1.5 mL, excess). The mixture was stirred for 30 minutes. A saturated ammonium sulfate solution (50 mL) and ethyl acetate (50 mL) was added. The organic layer was separated and aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4), evaporated to yield the title compound as a white solid (0.35 g, 87%): mp 63-64° C.; 1H-NMR (DMSO-d6) δ 7.90 (m, 2H), 7.62 (d, 1H, J=7.7 Hz), 7.58 (d, 1H, J=7.7 Hz), 7.40 (m, 2H), 7.29-7.32 (m, 3H), 7.14 (dd, 1H, J=8.1, 1.9 Hz), 7.01-7.04 (m, 2H), 6.33 (d, 1H,J=4.3 Hz), 5.31 (q, 1H, J=5.8 Hz), 4.88 (dd, 1H, J=10.8, 5.0 Hz), 4.65 (dd, 1H, J=10.8, 4.6 Hz), 4.34 (t, 1H, J=4.6 Hz), 3.71 (s, 3H), 1.52 (s, 3H), 1.21 (s, 3H), 1.06 (d, 3H, J=5.4 Hz); MS (ESI) m/z 504 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. extractionaqueous layer was extracted with ethyl acetate (3×15 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1e0533d8860e43b896550021da84a491
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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