2-Methyl-2-butene → HCID 68672018, compound

HRID 571913Notes

Reaction equation

HRID 571913 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]=[C:9]2[NH:34][C:35](=[O:45])[C:36]1[CH:41]=[C:40]([CH:42]=[O:43])[CH:39]=[CH:38][C:37]=1[F:44].CC(=CC)C.Cl([O-])=[O:56].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:46]=[C:47]([F:49])[CH:48]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[N:10]=[C:9]2[NH:34][C:35](=[O:45])[C:36]1[CH:41]=[C:40]([CH:39]=[CH:38][C:37]=1[F:44])[C:42]([OH:56])=[O:43]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86647620HCID 86647620, compound

Product 1

HCID 68672018HCID 68672018, compoundYield 117.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[5-(3,5-Difluoro-benzyl)-1-trityl-1H-indazol-3-yl]-2-fluoro-5-formyl-benzamide (88 mg, 0.135 mmol) in tert-butanol (1.8 mL) at room temperature was treated first with 2-methyl-2-butene (0.079 mL, 1.082 mmol) and then with sodium chlorite (37 mg, 0.405 mmol) and sodium dihydrogenphosphate in water (0.8 mL) drop-wise. The reaction was stirred over-night, EtOAc was then added (30 mL) and washed with water (25 mL). The aqueous layer was extracted twice with EtOAc (2×10 mL). The combined organic layers were washed with brine, evaporated to dryness to leave 106 mg of title compound which was employed in the following step with no need of further purification.

Workup

  1. washwashed with water (25 mL)
  2. extractionThe aqueous layer was extracted twice with EtOAc (2×10 mL)
  3. washThe combined organic layers were washed with brine
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-48147f3b10fa4cb4b3849c3c3f67a363
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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