HCID 57431666, compound → HCID 57431667, compound

HRID 545545Notes

Reaction equation

HRID 545545 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Br:21])[CH:17]=3)[N:12]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:11]=2[CH2:10][CH2:9]1)(C)(C)C>Cl.O1CCOCC1>[Br:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[C:11]1[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:20][C:19]2=1

Participants

4

Reactant 1

HCID 57431666HCID 57431666, compound

Product 1

HCID 57431667HCID 57431667, compoundYield 109.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To remove the —BOC protecting group, dissolve [6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-carbamic acid tert-butyl ester (6.0 mg, 12.7 mmol) in 4N HCl in dioxane (100 mL). Stir for 10 min and then add more dioxane (50 mL) to aid in stirring the thick white solid. Collect the solid and wash with diethyl ether to give 5.2 g (99%) 6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylamine as the HCl salt. MS (ES): m/z 356, 358 (M+1); HPLC: Rt=1.84 min, (96%).

Workup

  1. customTo remove the —BOC protecting group
  2. stirringin stirring the thick white solid
  3. customCollect the solid
  4. washwash with diethyl ether

Sources & evidence

ORD record
ord-ba446001bd2548508985db7d544c7905
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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