3-(2-Bromoethyl)indole → HCID 66932497, compound

HRID 2046732Notes

Reaction equation

HRID 2046732 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:13][O:14][C:15](=[O:41])/[CH:16]=[CH:17]/[C:18]1[CH:19]=[C:20]2[C:37](=[CH:38][CH:39]=1)[O:36][C:23]1([CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]1)[CH2:22][C:21]2=[O:40]>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:41])/[CH:16]=[CH:17]/[C:18]1[CH:19]=[C:20]2[C:37](=[CH:38][CH:39]=1)[O:36][C:23]1([CH2:24][CH2:25][N:26]([CH2:2][CH2:3][C:4]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[NH:6][CH:5]=3)[CH2:27][CH2:28]1)[CH2:22][C:21]2=[O:40]

Participants

4

Reactant 2

HCID 769243-(2-Bromoethyl)indoleHCID 52952087(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid methyl ester2×

Product 1

HCID 66932497HCID 66932497, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.46 ml, 3.3 mmol) and 3-(2-bromoethyl)-1H-indole (193 mg, 0.863 mmol) were added to a suspension of (E)-3-{4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester hydrochloride (220 mg, 0.66 mmol, Intermediate 1) in DCM (5 ml), and the mixture was stirred at RT overnight. DCM was evaporated and the residue was dissolved in DMF and heated at 60° C. overnight. The mixture was partitioned between water and AcOEt and the aqueous phase was extracted with DCM. The collected organic phases were dried over Na2SO4 and evaporated. The crude mixture was purified by column chromatography (eluent:DCM/MeOH/NH4OH 94:6:0.2) to give (E)-3-{1′-[2-(1H-indol-3-yl)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (130 mg).

Workup

  1. customDCM was evaporated
  2. dissolutionthe residue was dissolved in DMF
  3. temperatureheated at 60° C. overnight
  4. customThe mixture was partitioned between water and AcOEt
  5. extractionthe aqueous phase was extracted with DCM
  6. dry with materialThe collected organic phases were dried over Na2SO4
  7. customevaporated
  8. customThe crude mixture was purified by column chromatography (eluent:DCM/MeOH/NH4OH 94:6:0.2)

Sources & evidence

ORD record
ord-17437cb6c8294f088138069295e7d203
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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