(2,4-Dichlorophenyl)boronic acid → HCID 23518414, compound

HRID 1836588Notes

Reaction equation

HRID 1836588 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:14]=[C:15]2[C:20]3=[C:21]([CH2:23][CH2:24][N:19]3[CH2:18][C@@H:17]3[CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][C@H:16]23)[CH:22]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[C:15]2[C:20]3=[C:21]([CH2:23][CH2:24][N:19]3[CH2:18][C@@H:17]3[CH2:25][NH:26][CH2:27][C@H:16]23)[CH:22]=1

Participants

3

Reactant 2

HCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 131724548HCID 131724548, compound

Product 1

HCID 23518414HCID 23518414, compound

Procedure

Using 2,4-dichlorobenzeneboronic acid and following the procedures described in EXAMPLE 20, (±)-cis tert-butyl 2-bromo-4,5,7a,8,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline-9(7H)-carboxylate was converted into (±)-cis-2-(2,4-dichlorophenyl)-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline, trifluoroacetic acid salt, after HPLC purification (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA). This material was free-based with aq ammonium hydroxide, extracted with chloroform, washed with brine, dried (K2CO3) and concentrated to the title compound of EXAMPLE 112 as the free base. 1H NMR (CDCl3) δ: 7.46 (d, 1H, J=2.2 Hz), 7.29-7.20 (m, 2H), 7.05 (d, 1H, J=1.1 Hz), 6.93 (d, 1H, J=0.8 Hz), 3.58 (dd, 1H, J=10.9, 7.7 Hz ), 3.50-3.30 (m, 4H), 3.15-2.95 (m, 5H), 2.90-2.77 (m, 2H). LRMS (ES)+: 345.2 (M+H)+.

Workup

  1. customafter HPLC purification (C18
  2. washphase column, elution with a H2O/CH3CN gradient with 0.5% TFA)
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated to the title compound of EXAMPLE 112 as the free base

Sources & evidence

ORD record
ord-37bd41f6747d4918aa20f423dd6f6e06
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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