Tetrahydrofuran → HCID 58205021, compound

HRID 1799840Notes

Reaction equation

HRID 1799840 reaction equation
C([Mg]Cl)(C)C.O1CCCC1.I[C:12]1[N:13]=[C:14]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:24][C:19]=3[O:18][CH2:17][CH2:16][N:15]2[CH:29]=1.[CH2:30]([Sn:34](Cl)([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33].[NH4+].[Cl-]>>[CH2:39]([Sn:34]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:35][CH2:36][CH2:37][CH3:38])[C:12]1[N:13]=[C:14]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:24][C:19]=3[O:18][CH2:17][CH2:16][N:15]2[CH:29]=1)[CH2:40][CH2:41][CH3:42]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 58204516Methyl 2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 58205021HCID 58205021, compound

Procedure

Isopropylmagnesium chloride in tetrahydrofuran (2.0 M, 1.5 mL, 3.00 mmol) was added dropwise to a solution of methyl 2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (740 mg, 2.00 mmol) in Tetrahydrofuran (12 mL, 150 mmol) at room temperature. The mixture was stirred for 2.5 hours. Tributyltin chloride (0.8138 mL, 3.000 mmol) was added and the mixture was stirred for 18 hours. The mixture was mixed with sat aq. NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and purified on 25 g silica column eluting with 15-20% ethyl acetate in heptane. Yield 160 mg (15%). MS (ESI+): 535.2

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified on 25 g silica column
  6. washeluting with 15-20% ethyl acetate in heptane

Sources & evidence

ORD record
ord-fc78753f7031439ea435a3b1f25cfa58
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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