Hydrochloric Acid → HCID 178505846, compound

HRID 394593Notes

Reaction equation

HRID 394593 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH:7]=[CH:6]2)#[CH:2].[N:19]([Si](C)(C)C)=[N+:20]=[N-:21].[OH-].[Na+].Cl>ClCCl>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([C:1]4[N:19]=[N:20][NH:21][CH:2]=4)=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 78378AzidotrimethylsilaneHCID 10977406HCID 10977406, compound

Product 1

HCID 178505846HCID 178505846, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 5-ethynyl-1-(4-fluorophenyl)-1H-indole (9.6 g) and neat azidotrimethylsilane (21.7 g) was heated in a sealed tube at 170° C. for 24 h. The reaction mixture was cooled to 0° C. and a mixture of dichloromethan (150 mL) and 2 N aqueous sodium hydroxide was added. After stirring at room temperature for 2 h, the mixture was acidified with concentrated hydrochloric acid. The phases were separated and the aqueous phase was extracted with dichloromethane (2×200 mL). The combined organic phases were washed with brine (200 mL), dried (MgSO4) and the volatile solvents evaporated in vacuo affording pure title compound 19a as an oil (11.8 g): 1H NMR (CDCl3) δ 6.80 (d, 1H), 7.25 (t, 2H), 7.40 (d, 1H), 7.55 (dd, 2H), 7.60 (d, 1H), 7.75 (broad d, 1H), 8.05 (s, 1H), 8.20 (broad s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionwas added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with dichloromethane (2×200 mL)
  5. washThe combined organic phases were washed with brine (200 mL)
  6. dry with materialdried (MgSO4)
  7. customthe volatile solvents evaporated in vacuo

Sources & evidence

ORD record
ord-1ea8051c0d1a467193e0ef722b5906ba
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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