Tributyltin azide → HCID 178420226, compound

HRID 1349681Notes

Reaction equation

HRID 1349681 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#[N:17])=[CH:13][CH:14]=2)[C:9]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8]1.[N:26]([Sn](CCCC)(CCCC)CCCC)=[N+:27]=[N-:28]>C1(C)C=CC=CC=1>[C:20]1([CH2:19][CH2:18][C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[C:12]([C:16]4[N:17]=[N:26][NH:27][N:28]=4)[CH:11]=3)[NH:7][N:8]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 22479794HCID 22479794, compound

Product 1

HCID 178420226HCID 178420226, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared as described in Example 167, using 1-perhydro-2H-pyran-2-yl-3-(2-phenylethyl)-1H-indazole-5-carbonitrile (0.117 g, 0.35 mmol), azidotributyl tin (0.353 g, 0.292 mL, 1.06 mmol) in toluene (5 mL). After hydrolysis of the protecting group under acidic conditions, the compound was purified by acid/base extraction. The residue was partitioned between 6.0N NaOH and ethyl acetate. The aqueous phase was then acidified with 6.0 N aqueous hydrogen chloride, to pH 3–4, resulting in the formation of a white precipitate that was collected by filtration, washed with small portions of cold water and dried under vacuum (0.038 g, 37% yield over 2 steps): 1H NMR (DMSO-d6) δ 13.05 (br s, 1H), 8.5 (s, 1H), 8.0 (d, 1H), 7.65 (d, 1H), 7.3 (m, 4H), 7.15 (m, 1H), 3.3 (m, 2H), 3.1 (m, 2H); ES-MS (m/z) 291 [M+1]+.

Workup

  1. customAfter hydrolysis of the protecting group under acidic conditions
  2. customthe compound was purified by acid/base extraction
  3. customThe residue was partitioned between 6.0N NaOH and ethyl acetate
  4. customresulting in the formation of a white precipitate that
  5. filtrationwas collected by filtration
  6. washwashed with small portions of cold water
  7. customdried under vacuum (0.038 g, 37% yield over 2 steps)

Sources & evidence

ORD record
ord-bd6eccdd35414a9d9ffbc3cca673857d
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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