Hydrochloric Acid → HCID 45279721, compound

HRID 2060742Notes

Reaction equation

HRID 2060742 reaction equation
Cl[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([C:18]([OH:20])=[O:19])[C:10](=[O:17])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:4][CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C1COCC1.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([C:18]([OH:20])=[O:19])[C:10](=[O:17])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 45279720HCID 45279720, compound

Product 1

HCID 45279721HCID 45279721, compound

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(4-chlorobenzyl)-4-oxo-4H-quinolizine-3-carboxylic acid (0.060 g, 0.19 mmol) in 2 mL of THF under N2(g) was added phenylboronic acid (0.035 g, 0.29 mmol), 1 N cesium carbonate (0.38 mL, 0.38 mmol), and bis (tri-tert-butylphosphine) palladium(0). The reaction was heated to 100° C. for 15 h, cooled to rt, and acidified with 6 N HCl to pH ˜3. The mixture was then filtered and subjected to purification via reverse phase HPLC to yield the title compound that gave a mass ion (ES+) of 356.0 for M+H+. 1H NMR (400 MHz, d6-DMSO) δ 9.40 (d, J=7.2 Hz, 1H), 8.41 (s, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.09-8.05 (m, 1H), 7.69 (d, J=6.9 Hz, 1H), 7.63-7.58 (m, 4H), 7.46-7.42 (m, 2H), 7.35-7.33 (m, 3H), 4.39 (s, 2H).

Workup

  1. temperaturecooled to rt
  2. filtrationThe mixture was then filtered
  3. customsubjected to purification via reverse phase HPLC

Sources & evidence

ORD record
ord-9f57df77bbe34dd4b7baae4449e437b5
Source dataset
uspto-grants-2012_10
Patent number
US08278453B2

Reaction notes

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