Ammonium Hydroxide → HCID 58932529, compound

HRID 853892Notes

Reaction equation

HRID 853892 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][N:15]=[C:7]3[C:6]3(OCCC[O:16]3)[C:5]=2[CH:4]=1.B(Br)(Br)Br.[NH4+].[OH-]>C(Cl)Cl>[OH:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][N:15]=[C:7]3[C:6](=[O:16])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 58932576HCID 58932576, compound

Product 1

HCID 58932529HCID 58932529, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-75 °C

Procedure

To a cold solution of 8′-methoxy-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′pyrimido[1,2-a]indole] (0.723 g, 2.63 mmol) in anhyd. CH2Cl2 (26.4 mL) was added neat boron tribromide (0.80 mL, 8.43 mmol, 3.2 eq) drop-wise via syringe pump over a period of 55 min with cooling to −75° C. in a dry ice/iPrOH bath. The reaction was kept at about −18° C. for 13 hr then poured onto ice and neutralized to pH 7 with concentrated NH4OH keeping the reaction temperature <5° C. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated. The crude product was combined with the product (0.11 g) from a previous run and triturated with warm EtOAc and filtered to give the title compound as a dark red solid (0.178 g, 33% yield). NMR (300 Mz, DMSO-d6): consistent. MS: (APCI+) 203 [M+H].

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customtriturated with warm EtOAc
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c90e2a2fd6ee40ce91f6d5f57776d855
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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