Water → Tert-butyl 9'-(trifluoromethyl)spiro-[piperidine-4,6'-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate

HRID 2204085Notes

Reaction equation

HRID 2204085 reaction equation
[CH:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[C:7]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[O:6][C:5]=2[N:4]=[CH:3][CH:2]=1.[F:26][C:27]([F:42])([F:41])[S+]1C2C=CC=CC=2C2C=CC=CC1=2.O>CN(C=O)C>[F:26][C:27]([F:42])([F:41])[C:11]1[N:9]2[C:10]3[CH:1]=[CH:2][CH:3]=[N:4][C:5]=3[O:6][C:7]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:8]2=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27775055-(Trifluoromethyl)dibenzothiophen-5-iumHCID 58551499Tert-butyl spiro[piperidine-4,6'-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate

Product 1

HCID 67465074Tert-butyl 9'-(trifluoromethyl)spiro-[piperidine-4,6'-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl spiro[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate (134 mg, 0.393 mmol) and 5-(trifluoromethyl)dibenzothiophen-5-ium (99.4 mg, 0.393 mmol) in DMF (2 mL) was stirred at 80° C. for 1.5 hours. The mixture was poured into water and was extracted with EtOAc (3×). The organics were combined, washed with water and brine, dried (Na2SO4) and evaporated to dryness. The residue was purified by column chromatography (1-30% EtOAc/hexanes) to give tert-butyl 9′-(trifluoromethyl)spiro-[piperidine-4,6′-pyrido[2,3-b]pyrrolo[1,2-d][1,4]oxazine]-1-carboxylate (83 mg, 56%). ESI-MS m/z calc. 409.2, found 410.5 (M+1)+; Retention time: 1.92 minutes (3 min run).

Workup

  1. extractionwas extracted with EtOAc (3×)
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography (1-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-eb048c09d0a84dffb5fbac68e7e07180
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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