Methyl Carbamate → HCID 86609398, compound

HRID 1784860Notes

Reaction equation

HRID 1784860 reaction equation
ClC1C=[C:6]([C:8]([C:10]2[CH:15]=[C:14](Br)[CH:13]=[C:12](Br)[CH:11]=2)=O)C=CN=1.[CH3:18][O:19][C:20](=[O:38])[NH:21][C:22]1[CH:27]=[C:26]([C:28]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([Cl:36])[CH:31]=2)=[O:29])[CH:25]=[C:24](Br)[CH:23]=1.COC(=O)[NH2:42]>[Pd]>[CH3:18][O:19][C:20](=[O:38])[NH:21][C:22]1[CH:23]=[C:24]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:10]=2[CH:8]=[CH:6][NH:42]3)[CH:25]=[C:26]([C:28]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([Cl:36])[CH:31]=2)=[O:29])[CH:27]=1

Participants

5

Reactant 3

HCID 11722Methyl CarbamateHCID 50994269HCID 50994269, compoundHCID 86609399HCID 86609399, compound

Product 1

HCID 86609398HCID 86609398, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2-Chloro-pyridin-4-yl)-(3,5-dibromo-phenyl)-methanone was converted to [3-bromo-5-(2-chloro-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester under the palladium catalyzed conditions described for Example 86, using carbamic acid methyl ester in place of methanesulfonamide. The Suzuki reaction and removal of the triisopropylsilyl protecting group were carried out as described in Example 35. 1H NMR (400 MHz, CDCl3): δ 8.56 (d, J=4.9 Hz, 1H), 8.35 (s, 1H), 8.07 (s, 1H), 7.82 (s, 1H), 7.77 (t, J=1.5 Hz, 1H), 7.69 (s, 1H), 7.55 (dd, J=5.0, 1.3 Hz, 1H), 7.43 (d, J=8.2 Hz, 1H), 7.30-7.25 (m, 2H), 7.18 (dd, J=7.2, 0.8 Hz, 1H), 6.85 (s, 1H), 6.71 (s, 1H), 3.81 (s, 3H).

Sources & evidence

ORD record
ord-36127330c5584e7fa7702fe68790e3b4
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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