Sodium Carbonate → HCID 24990697, compound

HRID 222134Notes

Reaction equation

[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3[C:14]([C:15]([NH2:17])=[O:16])=[C:13](I)[N:12]([CH3:19])[C:9]=32)=[CH:4][N:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:12]([CH3:19])[C:9]=32)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 8-amino-2-iodo-1-methyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid amide N3 (0.34 mmol) in 15 mL of DMF under argon, phenylboronic acid (0.5 mmol), LiCl (1 mmol), Na2CO3 (0.85 mmol), water (1 mL) and (PPh3)2PdCl2 (7 mg) were added. The mixture was heated at 100° C. for 10 h then evaporated to dryness. Chromatography on silica gel (eluant: DCM/MeOH 20:1) afforded the title compound (74% yield). ESI (+) MS: m/z 320 (MH+). 1H NMR: 2.68 (t, J=7.80, 2H), 2.84 (t, J=7.80, 2H), 3.86 (s, 3H), 6.21 (bs, 2H), 6.27 (bs, 1H), 6.91 (bs, 1H), 7.41-7.54 (m, 5H), 7.99 (s, 1H).

Workup

customthen evaporated to dryness

Sources & evidence

ORD record: ord-f0438b3588564b36971d635e36888739
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207180B2

Reaction notes

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