4,6-Bis[trifluoromethyl]-1,3,3-trimethyl-2-methylenepyrrolo[2,3-b]pyridine → 4,6-bis[trifluoromethyl]-1,3,3-trimethyl-6'-piperidinospiro[2H-pyrrolo[2,3-b]pyridine-2,3'-[3H]-[2H-[1,4]benzoxazino[6,5-b]benzofuran]]

HRID 355610Notes

Reaction equation

HRID 355610 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[C:5]2[N:13]([CH3:19])[C:14](=[CH2:18])[C:15]([CH3:17])([CH3:16])[C:4]=12.[OH:22][C:23]1[CH:35]=[C:34]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[C:26]2[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:25]=2[C:24]=1[N:42]=O>C1(C)C(C)=CC=CC=1>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[N:6]=[C:5]2[N:13]([CH3:19])[C:14]3([C:15]([CH3:16])([CH3:17])[C:4]=12)[CH2:18][NH:42][C:24]1[C:25]2[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][C:26]=2[C:34]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:35][C:23]=1[O:22]3

Participants

4

Reactant 2

HCID 189401524,6-Bis[trifluoromethyl]-1,3,3-trimethyl-2-methylenepyrrolo[2,3-b]pyridineHCID 189401542-Hydroxy-1-nitroso-4-piperidinodibenzofuran2×

Product 1

HCID 538249694,6-bis[trifluoromethyl]-1,3,3-trimethyl-6'-piperidinospiro[2H-pyrrolo[2,3-b]pyridine-2,3'-[3H]-[2H-[1,4]benzoxazino[6,5-b]benzofuran]]

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4,6-bis[trifluoromethyl]-1,3,3-trimethyl-2-methylenepyrrolo[2,3-b]pyridine (1.83 g; 0.0059 mol) and 2-hydroxy-1-nitroso-4-piperidinodibenzofuran (2.60 g; 0.01 mol) in xylene (50 ml) was stirred and heated under nitrogen and refluxed for 24 hours. A further portion of 2-hydroxy-1-nitroso-4-piperidinodibenzofuran (1.2 g; 0.0059 mol) was added and the reaction continued for a further 24 h. The resulting dark solution was evaporated to dryness and the resulting gum chromatographed over silica (eluent: 2% diethyl ether in petroleum ether 60/80) to give 4,6-bis[trifluoromethyl]-1,3,3-trimethyl-6'-piperidinospiro[2H-pyrrolo[2,3-b]pyridine-2,3'-[3H]-[2H-[1,4]benzoxazino[6,5-b]benzofuran]] as an orange solid (0.08 g; 3%), m.pt. 195°-205° C., λmax absorbance 498 nm (polyurethane). ##STR28##

Workup

  1. temperatureheated under nitrogen
  2. temperaturerefluxed for 24 hours
  3. customThe resulting dark solution was evaporated to dryness
  4. customthe resulting gum chromatographed over silica (eluent: 2% diethyl ether in petroleum ether 60/80)

Sources & evidence

ORD record
ord-bf04637ec4ba4dcdaa7eb0f04aea4c79
Source dataset
uspto-grants-1998_11
Patent number
US05833885

Reaction notes

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